JPS5890579A - Preparation of vinyl sulfide - Google Patents
Preparation of vinyl sulfideInfo
- Publication number
- JPS5890579A JPS5890579A JP13001582A JP13001582A JPS5890579A JP S5890579 A JPS5890579 A JP S5890579A JP 13001582 A JP13001582 A JP 13001582A JP 13001582 A JP13001582 A JP 13001582A JP S5890579 A JPS5890579 A JP S5890579A
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- phenyl
- parts
- alkyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 title 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 10
- -1 (substituted)phenyl Chemical group 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 5
- VCZKTIKPEDMZNW-UHFFFAOYSA-N O=S(=O)=S Chemical class O=S(=O)=S VCZKTIKPEDMZNW-UHFFFAOYSA-N 0.000 abstract description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract description 3
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000008127 vinyl sulfides Chemical class 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 8
- 238000005292 vacuum distillation Methods 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GASBKMMGAZYXQD-UHFFFAOYSA-N benzhydrylbenzene;sodium Chemical compound [Na].C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 GASBKMMGAZYXQD-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- KFSUURZPFXKUAI-UHFFFAOYSA-N benzhydrylbenzene;lithium Chemical compound [Li].C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 KFSUURZPFXKUAI-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- UPQNPBHYPACBSK-UHFFFAOYSA-N methylsulfinylmethane;sodium Chemical compound [Na].CS(C)=O UPQNPBHYPACBSK-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- NCFSDGWPAKOPOU-UHFFFAOYSA-N n-ethylethanamine;lithium Chemical compound [Li].CCNCC NCFSDGWPAKOPOU-UHFFFAOYSA-N 0.000 description 1
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、医薬品、香料等の合成中間体やそれ自身モノ
マー、コモノマー等として有用す、 ビニルスルフィ
ド類の新規製造法に係る。詳記すれば、Ｎ−置換スルホ
ニルスルフィルイミン類ト強塩基とを反応させる。ビニ
ルスルフィド類の新規製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a new method for producing vinyl sulfides, which are useful as synthetic intermediates for pharmaceuticals, fragrances, etc., or as monomers, comonomers, etc. themselves. Specifically, N-substituted sulfonylsulfilimines are reacted with a strong base. This article relates to a new method for producing vinyl sulfides.
従来ビニルスルフィド類の製法としては、グロピオフェ
ノンとチオフェノールとを反応させる方法やハーフイペ
リノト又はイペリットを脱ハロゲ収率が悪く、後者は７
、収率が低いと共に原料の毒性が極めて高い等の欠点が
あり、いずれも工業的製法としては不満足であった。Conventional methods for producing vinyl sulfides include a method in which glopiophenone and thiophenol are reacted, and a method in which half-ipelinot or ipelite has a poor dehalogenation yield, and the latter has a low yield of 7
However, these methods have drawbacks such as low yield and extremely high toxicity of raw materials, and both are unsatisfactory as industrial production methods.
本発明者等は鋭意検討し、Ｎ−置換スルホニルスルフィ
ド類を強塩基と反応させることにより、ノ
緩和な条件下、容易に所望のビニルスルフィド類を高収
率で製造し得る１本発明を完成した。The inventors of the present invention have conducted intensive studies and completed the present invention, which enables the production of desired vinyl sulfides in a high yield easily under mild conditions by reacting N-substituted sulfonyl sulfides with a strong base. did.
本発明に使用する原料Ｎ−置換スルホニルスル、アルキ
ル、フェニル、置換フェニル、アラルキル、置換アラル
キル、ビニル、置換ビニル基を、Ｒ２はアルキル、置換
アルキル、アリール、置換アＲ４＋ Ｒｓハ、水素、ア
ルキル、置換アルキル、フェニル、Ｒ換：ｙエニル、シ
クロアルキル、置換シクロアルキル、ビニル、置換ビニ
ル基ヲ示す。又ＲＪりて珈を形成する場合をも含む。）
なる化合物で、例えば、Ｓ−２二ニル−８−イングロビ
ルーＮ−Ｐ〜トシルスルフィルイミンｉ ｓ フェニル
−８−エチル−Ｎ−メシルスルフィルイミン、Ｓ−７エ
ニルーＳ−シクロへキシル−Ｎ−Ｐ−トシルスルフィル
イミン、Ｓ−フェニル−８〜（１−フェニルプロピル）
−Ｎ−Ｐ ）シルスルフィルイミン、Ｂ−フェニル
−８−（２−：ｙエニルエチル）−Ｎ−メシルスルフィ
ルイミン、８−メチル−Ｓ−エチル−Ｎ −Ｐ ＋ ト
シルスルフィルイミン、”＋” −ジエチル−Ｎ −Ｐ
−）シルスルフィルイミン、Ｓ〜エチル−８−プロピ
ル−Ｎ −Ｐ ＋＋ ）シルスルフィルイミン、Ｓ−エ
チル−８−イソプロピル−Ｎ−、、ＰＨトシルスルフィ
ルイミンＳ−エチル−８−（１−、ｙエニルエチ／１．
） −Ｎ−−メシルスルフィシイミン、８−ベンジル
−８−エチル＋ Ｎ −Ｐ −） シ／ｌ／ ｘルフイ
ルイミン、Ｂ−ペンシル−５−４ソプロピルーＮ−メシ
ルスルフィルイミン、５−Ｐ−）シル−８−（１−フェ
ニルエチル）−Ｎ−Ｐ−）シルスルフィルイミン、Ｎ−
Ｐ−トシルペンタメチレンスルフィルイミン、ｓ−エチ
ル−８−シクロヘキシル−Ｎ−Ｐ−トシルスルフィルイ
ミン等が挙げられる。。The raw materials used in the present invention are N-substituted sulfonylsulfur, alkyl, phenyl, substituted phenyl, aralkyl, substituted aralkyl, vinyl, substituted vinyl group, R2 is alkyl, substituted alkyl, aryl, substituted aR4+ Rs, hydrogen, alkyl, Substituted alkyl, phenyl, R-substituted: yenyl, cycloalkyl, substituted cycloalkyl, vinyl, substituted vinyl group. It also includes the case where RJ is formed. )
For example, S-2dynyl-8-ingrobi-N-P~tosylsulfilimine is phenyl-8-ethyl-N-mesylsulfilimine, S-7enyl-S-cyclohexyl-N- P-tosylsulfilimine, S-phenyl-8-(1-phenylpropyl)
-N-P) silsulfilimine, B-phenyl-8-(2-:yenylethyl)-N-mesylsulfilimine, 8-methyl-S-ethyl-N-P + tosylsulfilimine, "+ ”-diethyl-N-P
-) silsulfilimine, S~ethyl-8-propyl-N -P ++) silsulfilimine, S-ethyl-8-isopropyl-N-,, PH tosylsulfilimine S-ethyl-8-(1 -, y enylethyl/1.
) -N--Mesylsulficimine, 8-benzyl-8-ethyl + N-P-) C/l/x rufilimine, B-pencil-5-4sopropyl-N-mesylsulfilimine, 5-P- ) sil-8-(1-phenylethyl)-N-P-) silsulfilimine, N-
Examples include P-tosylpentamethylenesulfilimine, s-ethyl-8-cyclohexyl-N-P-tosylsulfilimine, and the like. .
原料物質として用いる、Ｎ−置換スルホニルスルフィル
イミン類は、例えば、スルフィドとクロラミンＴよりの
公知の方法により合成される。The N-substituted sulfonylsulfilimines used as raw materials are synthesized, for example, from sulfide and chloramine T by a known method.
本発明に使用される強塩基としては、例えばポタシウム
ーｔ−ブトキシド、ナトリウムアミド。Examples of strong bases used in the present invention include potassium t-butoxide and sodium amide.
カリウムアミド、ナトリウムハイドライド、リチウムハ
イドライド、ナトリウムジメチルスルホキシド、リチウ
ムトリフェニルメタン、ナトリウムトリフェニルメタン
、ボタシウムトリフェニルメタン、ナトリウムナフタリ
ン、リチウムジエチルアミン、１，１−ジメチルーナト
リウームプロポキシド等が挙げられる。Potassium amide, sodium hydride, lithium hydride, sodium dimethyl sulfoxide, lithium triphenylmethane, sodium triphenylmethane, botanical triphenylmethane, sodium naphthalene, lithium diethylamine, 1,1-dimethylsodium propoxide and the like can be mentioned.
反応は好ましくは溶剤の存在下に、Ｎ−置換スルホニル
スルフィルイミン類と強塩基とを混合し、室温乃至必要
に応じて加温して行なわれる。The reaction is preferably carried out by mixing the N-substituted sulfonylsulfilimine and a strong base in the presence of a solvent and heating the mixture at room temperature or if necessary.
使用される反応溶剤としては、出発原料、強塩基の種類
等により異なるが、一般には、テトラヒドロフラン、ジ
オキサン、ジメチルホルム了ミド、ベンゼン、トルエン
、１．２−ジメトキシエタン、ジエチルエーテル等が使
用される。The reaction solvent used varies depending on the starting materials, the type of strong base, etc., but generally tetrahydrofuran, dioxane, dimethylformide, benzene, toluene, 1,2-dimethoxyethane, diethyl ether, etc. are used. .
反応終了後、反応液より生成物？単離するには、例えば
、反応液に水を加え、溶媒抽出し、蒸留又はクロマトグ
ラフィー等により分離、精製される。After the reaction is complete, is there a product from the reaction solution? For isolation, for example, water is added to the reaction solution, solvent extraction is performed, and separation and purification is performed by distillation, chromatography, or the like.
本発明によって得られるビニルスルフィド類は、化合物
によっては２種の幾何異性体が得られ、生成するビニル
スルフィド類中におけるこれら異性体の組成比は、化合
物の種類によって異なるが、得られたビニルスルフィド
類を、核磁気共鳴スベクトル、赤外線スペクト４ル及び
カスクロマトクラフィー等の分析手段によって分析すれ
ば、その組成比は容易に求められる。The vinyl sulfides obtained by the present invention can be obtained as two types of geometric isomers depending on the compound, and the composition ratio of these isomers in the vinyl sulfides produced varies depending on the type of compound, but the vinyl sulfides obtained The composition ratio can be easily determined by analyzing the same using analytical means such as nuclear magnetic resonance spectrum, infrared spectrum, and gas chromatography.
以上述ぺ＾如く本発明方法は、緩和な条件で、高収率で
ビニルスルフィド類の提供？可能とするものであり、斯
業に貢献する処極めて大きい。As mentioned above, the method of the present invention provides vinyl sulfides in high yield under mild conditions. The contribution it makes to this industry is enormous.
以下に実施例？挙げ、本発明を更に説明する。Examples below? The present invention will be further explained.
実施例中敷量ｒ表わす部は重量部である。Examples Insole amount r The parts expressed are parts by weight.
参考例Ｉ。Reference example I.
Ｓ−フェニル−８−イソプロピル−Ｎ−Ｐ−）シルスル
フィルイミン３２ 部ｔ”ベンゼン２００部に溶解し、
ザタシウムーｔ−ブトキシド５６部？加え、室温１０時
間反応し、反応液を水中にあけて、ベンゼン層金分取後
ベンゼン留去し、減圧蒸留によりす、Ｄ、２０７〜２０
８℃の留分１３部金得た。32 parts of S-phenyl-8-isopropyl-N-P-)silsulfilimine dissolved in 200 parts of benzene,
56 parts of Zatacium t-butoxide? Addition, react at room temperature for 10 hours, pour the reaction solution into water, separate the benzene layer gold, distill off the benzene, and perform vacuum distillation, D, 207-20
Thirteen parts of gold were obtained as a fraction at 8°C.
同様の方法により、下表の出発原料を用いて行つた結果
は下表の如くであつ几。The same method was carried out using the starting materials shown in the table below, and the results were as shown in the table below.
参考例２゜
Ｓ−フェニル−８−（１−フェニルプロピル）−Ｎ−Ｐ
−）シルスルフィルイミン４０部（ｚテトラヒドロフラ
ン２００部に溶解し、ナトリウムフッ４１２１部？加え
、３０〜３５°Ｃ７時間反応した。反応液に水と加え、
分液後、溶媒留去し、融点４２．５°Ｃの結晶１９部Ｈ
昧。Reference example 2゜S-phenyl-8-(1-phenylpropyl)-NP
-) 40 parts of silsulfilimine (z dissolved in 200 parts of tetrahydrofuran, 4121 parts of sodium fluoride was added, and reacted at 30-35°C for 7 hours. Added water to the reaction solution,
After separation, the solvent was distilled off, and 19 parts of crystals with a melting point of 42.5°C were obtained.
vague.
同様の方法により、出発原料を変えて行った結下は下表
の如くであった。The results obtained using the same method but using different starting materials were as shown in the table below.
以下余白
参考例 ３
Ｓ−ベンジル−８−（１−フェニルエチル）−Ｎ−メシ
ルスルフィルイミン３２ 部’ｔ １ ＋ ２−ジメト
キシエタン１８０部に溶解し、ナトリウムノ・イドライ
ド１０部金加え、２０〜３０°Ｃ８時間反応し友。実施
例１と同様に減圧蒸留により精製してす、ｐ、１８３〜
４°Ｃ／ １２ ＋ｏ＋Ｈｇの留分１９部と得たＯ
同様の方法により、出発原料を変えて行った結果は下表
の如くであつ九。Below is a margin reference example 3 S-benzyl-8-(1-phenylethyl)-N-mesylsulfilimine 32 parts 't 1 + Dissolved in 180 parts of 2-dimethoxyethane, added 10 parts of sodium hydride, 20 parts React at ~30°C for 8 hours. Purified by vacuum distillation in the same manner as in Example 1, p. 183~
19 parts of a fraction of 4°C/12+o+Hg and O obtained The results obtained using the same method but using different starting materials are as shown in the table below.
参考例４゜
Ｓ−フェニル−８−（２−フェニルエチル）−Ｎ−Ｐ−
トンルスルフイルイミン３９ 部ｅジエチルエーテル２
００部に溶解し、ナトリウムトリフェニルメタン１４０
部？加えて、３０−３５℃６時間反応した。実施例１と
同様にして、減圧蒸留により精製して、ｂ、ｏ、ｉ ５
５−１６０℃、／１閣Ｈｇの留分１６．５部？得た。Reference example 4゜S-phenyl-8-(2-phenylethyl)-NP-
Tontrusulfyl imine 39 parts e diethyl ether 2
00 parts of sodium triphenylmethane dissolved in 140 parts
Department? In addition, the reaction was carried out at 30-35°C for 6 hours. Purified by vacuum distillation in the same manner as in Example 1 to obtain b, o, i 5
5-160℃, 16.5 parts of distillate/1 kakuHg? Obtained.
同様の方法により、出発原料金変えて行った結果は下表
の如くであった。The same method was used, but the starting material charges were changed, and the results were as shown in the table below.
特許出願人 和光純薬工業株式会社
手続補正書
２５
昭和５７年８月丼日
特許庁長官 殿
１、事件の表示
ビニルスルフィド類の製法
３、補正をする者
事件との関係 特許出願人
郵便番号 ５４１
− Ｆノ１９寸 チーウメ パンチ住所 大阪府大
阪市東区道修町３丁目１０番地連絡先 特許課（東京）
＠ ０３−２７０−８５７１昭和５７年８月＃日
５、 補正の対象
明細書の発明の詳細な説明の欄０
６、補正の内容
（１１明細書９頁１０行目に記載の「実施例１」を「参
考例１」と補正する。Patent Applicant: Wako Pure Chemical Industries, Ltd. Procedural Amendment 25 August 1980, Japan Patent Office Commissioner, 1, Indication of the case Process for producing vinyl sulfides 3, Person making the amendment Relationship to the case Patent applicant postal code 541 − F19cm Chiume Punch Address: 3-10 Doshomachi, Higashi-ku, Osaka-shi, Osaka Contact information: Patent Division (Tokyo)
@ 03-270-8571 August #Date 5, 1982, Detailed explanation of the invention column 0 of the specification subject to amendment " shall be corrected to "Reference Example 1."
（２）明細書１０頁６行目に記載の「実施例１」を「参
考例１」と補正する。(2) "Example 1" written on page 10, line 6 of the specification is amended to "Reference Example 1."
以上 手続補正書（方式） ％式％ １、事件の表示 昭和５７年特許願第１３００１５号 ２、発明の名称 ビニルスルフィド類の製法 ３、補正をする者 事件との関係 特許出願人 ５、 補正の対象 明細書（８，９及び１０頁）。that's all Procedural amendment (formality) %formula% 1.Display of the incident 1981 Patent Application No. 130015 2. Name of the invention Manufacturing method of vinyl sulfides 3. Person who makes corrections Relationship to the case Patent applicant 5. Subject of correction Specification (pages 8, 9 and 10).
６、 補正の内容
明細書（８，９及び１０頁）の浄書（内容に変更なし）
。6. Engraving of the statement of contents of the amendment (pages 8, 9 and 10) (no changes to the contents)
.
別紙の通り。As per attached sheet.
以上 つた結果は下表の如くであった。that's all The results were as shown in the table below.
参考例２゜
Ｓ−フェニル−８−（１−フヱニルブロピル）−Ｎ−Ｐ
−）シルスルフィルイミン４０部をテトラヒドロフラン
２００部に溶解し、ナトリウムアマイド２１部を加え、
３０〜３５℃７時間反応した。反応液に水を加え、分液
後、溶媒留去し、融点４２．５℃の結晶１９部を得た。Reference example 2゜S-phenyl-8-(1-phenylpropyl)-NP
-) Dissolve 40 parts of silsulfilimine in 200 parts of tetrahydrofuran, add 21 parts of sodium amide,
The reaction was carried out at 30-35°C for 7 hours. Water was added to the reaction solution, and after liquid separation, the solvent was distilled off to obtain 19 parts of crystals with a melting point of 42.5°C.
同様の方法により、出発原料を変えて行った結下は下表
の如くであった。The results obtained using the same method but using different starting materials were as shown in the table below.
以下余白
参考例 ３
Ｓ−ベンジル−８−（１−フェニルエチル）−Ｎ−）シ
ルスルフィルイミン３２部を１，２−ジメトキシエタン
１８０部に溶解し、ナトリウムノ葛イドライド１０部を
加え、２０〜３０℃８時間反応した。実施例１と同様に
減圧蒸留により′精製してす、ｐ、１８３〜４℃／ １
２ ｓｍＨｇの留分１９部を得た。Below is a margin reference example 3. Dissolve 32 parts of S-benzyl-8-(1-phenylethyl)-N-)silsulfilimine in 180 parts of 1,2-dimethoxyethane, add 10 parts of sodium chloride hydride, The reaction was carried out at ~30°C for 8 hours. Purified by vacuum distillation in the same manner as in Example 1, p, 183-4°C/1
19 parts of a fraction of 2 smHg were obtained.
同様の方法により、出発原料を変え七行った結参考例４
Ｓ−フェニル−８−（２−フェニルエチル）−Ｎ−Ｐ−
）シルスルフィルイミン３９部をジエチルエーテル２０
０部に溶解し、ナトリウムトリフェニルメタン１４０部
を加えて、３０−３５℃６時間反応した。実施例１と同
様にして、減圧蒸留により精製して、ｂ、ｐ、１５５−
１６０℃／ＩＩ翼Ｈｇの留分１６．５部を得た。Seven experiments were carried out in the same manner using different starting materials.Reference Example 4 S-phenyl-8-(2-phenylethyl)-N-P-
) 39 parts of silsulfilimine to 20 parts of diethyl ether
0 parts, added 140 parts of sodium triphenylmethane, and reacted at 30-35°C for 6 hours. Purified by vacuum distillation in the same manner as in Example 1 to obtain b, p, 155-
16.5 parts of a 160°C/II blade Hg fraction was obtained.
同様の方法により、出発原料を変えて行った結果は下表
の如くであった。The same method was carried out using different starting materials, and the results were as shown in the table below.
Claims (1)
形成する。式中Ｒ’ｐｓアルキル、７エ二ル、置換フェ
ニル、アラルキル、置換アラルキル、・ビニル、置換ビ
ニル基を Ｒ２は、アルキル、置換アルキル、アリール
、置換アリール、シクロアルキル、置換シクロアルキル
基を、Ａは式−？Ｈ−＜’、 なる基を示し１式中Ｒ
”ｔ Ｒ’ｌ Ｒｓｕ、３ 水素、アルキル、置換アルキル、フェニル、置換フェニ
ル、シクロアルキル、置換シクロアルキル、ビニル、置
換ビニル基を示１゜又Ｒ３、Ｈ４，Ｒｓとがそれぞれ２
つずつ一緒になって積を形成する場−ス含む。〕なる化
合物と強塩基とを反応させるｎは１〜６の整数を示す。 ）なる化合物の製造方法。[Claims] Formula R-8-A ↓ N goi2· [In the formula, R1 and A together form a product. In the formula, R'ps is alkyl, 7enyl, substituted phenyl, aralkyl, substituted aralkyl, vinyl, substituted vinyl group, R2 is alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl group, A Is the expression −? H-<', represents a group in which R
"t R'l Rsu, 3 represents hydrogen, alkyl, substituted alkyl, phenyl, substituted phenyl, cycloalkyl, substituted cycloalkyl, vinyl, substituted vinyl group 1°, or R3, H4, Rs are each 2
This includes cases where each product is taken together to form a product. n represents an integer of 1 to 6. ).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13001582A JPS5890579A (en) | 1982-07-26 | 1982-07-26 | Preparation of vinyl sulfide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13001582A JPS5890579A (en) | 1982-07-26 | 1982-07-26 | Preparation of vinyl sulfide |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP145775A Division JPS5823391B2 (en) | 1974-12-30 | 1974-12-30 | vinyl sulfide inoseihou |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5890579A true JPS5890579A (en) | 1983-05-30 |
Family
ID=15024044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13001582A Pending JPS5890579A (en) | 1982-07-26 | 1982-07-26 | Preparation of vinyl sulfide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5890579A (en) |
-
1982
- 1982-07-26 JP JP13001582A patent/JPS5890579A/en active Pending
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